Jennifer Finney Boylan was born in Valley Forge, Pennsylvania (PA) in 1958, and she grew up by turns in Newton Square and Devon, PA.  Boylan attended the Haverford School, a private, all-boys preparatory school, from which she graduated in 1976. She often cites her father’s stoic, unfeeling brand of masculinity as the first contributing factor to her struggles with gender and emotions. She has even expressed the feeling that her father loved the family dog more openly than he loved his child. 

Boylan graduated from Wesleyan University with an English degree, and soon thereafter moved to New York and filled a position as managing editor for the magazine American Bystander. When American Bystander shut down in 1982, she became an editorial assistant at Viking Press for Penguin Random House, then later a production editor for the publisher EP Dutton. 

In 1985, Boylan’s career shifted from the publishing industry and into the academic world. She left EP Dutton and attended a graduate writing seminar at Baltimore’s Johns Hopkins University. Boylan became a Fellow in Literature of the Pennsylvania State Council on the Arts in 1987. By 1988, Boylan began working for Colby College in Maine as a professor of creative writing and American literature. She also married her wife, Deirdre (Deedie), and published her first book, a short story collection titled Remind Me to Murder You Later (1988), all in the same year. 

Boylan found her stride as a fiction writer. She received national acclaim for her novel The Planets (1991), and then again for its sequel The Constellations (1994). These works involve a group of people exploring Centralia, PA, and they are wild, inventive, inexplicable tales chock full of dark humor. She also published Getting In in 1997, another quirky and creative novel surrounding four high school students and a larger-than-life college admissions journey. 

It was around this time that Boylan truly began questioning her identity as a man. By 2000, Boylan had come out to her wife and mother as transgender, and began the long, slow process of transitioning. The next year, Boylan published her works under the name Jennifer, a significant moment in her social transition. While transitioning, Boylan feared for her marriage with Deedie, and there were certainly many rocky times to navigate. However, the couple worked together and persevered, and have been happily married for several decades at the time of this writing. 

Following her transition, Boylan became a very vocal transgender writer and activist, working hard to normalize and broaden the discussion around trans experiences. She published her first memoir, She’s Not There: A Life in Two Genders, in 2003 to extensive acclaim. It soon became the first bestselling work by a transgender American and is arguably her most well-known work. Boylan has appeared in connection with this work on several television shows, including The Oprah Winfrey Show and Larry King Live, as well as many college campuses and other speaking events. 

Boylan’s work expanded into transgender activism following this publication. She published memoirs and works about her experiences and was invited to speaking events involving transgender activism in general, independent of her written works. In 2010, she became a member of GLAAD, and in 2013 she was appointed as the organization’s first co-chair of the Board of Directors, a position she would hold until 2018. Boylan left her work as a professor at Colby in 2014, fully embracing her work as an author and activist. She appeared on the show I Am Cait in 2016, a series documenting her friend Caitlyn Jenner’s transition, as a co-star and consultant, and has also consulted for other shows, such as the Amazon series Transparent.  

At the time of this writing, Boylan lives at times in New York City and in Belgrade Lakes, Maine, with her wife, Deedie, and their two children, Sean and Zaira. She is the Anna Quindlen Writer in Residence and an English professor at Barnard College, where she continues to give a much-needed voice to transgender issues and acceptance.